Intramolecular iron-catalyzed transannulation of furans with O-acetyl oximes: synthesis of functionalized pyrroles
Literature Information
Publication Date
2021-10-05
DOI
10.1039/D1QO01281A
Impact Factor
5.281
Authors
Anton S. Makarov, Alexander A. Fadeev, Maxim G. Uchuskin
View Original
Abstract
Furyl-tethered O-acetyl oximes undergo a rearrangement to yield densely substituted pyrroles in the presence of FeCl3·6H2O. The reactivity of a furan ring resembles the behaviour of an activated olefin with a formal leaving group that reacts with electrophilic nitrogen in a 5-exo-trig manner to form a spiropyrroline intermediate followed by aromatization of pyrrole via an intermediate ring opening. In contrast to the common activation modes of O-acyl oximes that comprise homolysis, SET-reduction or oxidative addition of low-valent transition metal complexes across the N–O bond, in the present case the catalyst acts as a Lewis acid activating oxime nitrogen for a nucleophilic attack by the reaction partner. The studied reaction was integrated into a telescoping protocol for the synthesis of a broad range of pyrroles, which could find possible applications as flexible matrices for designing push–pull chromophores and as potential building blocks in organic chemistry.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
724
Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry
Recommended Compounds
4-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-yl)morpholine
CAS Number:
485799-04-0
Molecular Formula:
C15H23BN2O3
5,7,8'-Trihydroxy-2',2'-dimethyl-2'H,4H-3,6'-bichromen-4-one
CAS Number:
129280-33-7
Molecular Formula:
C20H16O6
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